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Details

Stereochemistry ACHIRAL
Molecular Formula C11H14N2O4
Molecular Weight 238.2399
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FELBAMATE

SMILES

NC(=O)OCC(COC(N)=O)C1=CC=CC=C1

InChI

InChIKey=WKGXYQFOCVYPAC-UHFFFAOYSA-N
InChI=1S/C11H14N2O4/c12-10(14)16-6-9(7-17-11(13)15)8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H2,12,14)(H2,13,15)

HIDE SMILES / InChI

Description

Felbamate is an antiepileptic indicated as monotherapy or as an adjunct to other anticonvulsants for the treatment of partial seizures resulting from epilepsy. Receptor-binding studies in vitro indicate that felbamate has weak inhibitory effects on GABA-receptor binding, benzodiazepine receptor binding, and is devoid of activity at the MK-801 receptor binding site of the NMDA receptor-ionophore complex. However, felbamate does interact as an antagonist at the strychnine-insensitive glycine recognition site of the NMDA receptor-ionophore complex. The mechanism by which felbamate exerts its anticonvulsant activity is unknown, but in animal test systems designed to detect anticonvulsant activity, felbamate has properties in common with other marketed anticonvulsants. In vitro receptor binding studies suggest that felbamate may be an antagonist at the strychnine-insensitive glycine-recognition site of the N-methyl-D-aspartate (NMDA) receptor-ionophore complex. Antagonism of the NMDA receptor glycine binding site may block the effects of the excitatory amino acids and suppress seizure activity. Animal studies indicate that felbamate may increase the seizure threshold and may decrease seizure spread. It is also indicated that felbamate has weak inhibitory effects on GABA-receptor binding, benzodiazepine receptor binding. Felbamate should be used only in those patients who respond inadequately to alternative treatments and whose epilepsy is so severe that a substantial risk of aplastic anemia and/or liver failure is deemed acceptable in light of the benefits conferred by its use. Felbatol is the brand name used in the United States for felbamate.

CNS Activity

Approval Year

PubMed

PubMed

TitleDatePubMed
Effects of anticonvulsant drugs on 4-aminopyridine-induced seizures in mice.
1992 Mar
Pharmacological characterization of the 6 Hz psychomotor seizure model of partial epilepsy.
2001 Dec
[Controversies about the new anti-epileptic drugs].
2001 Jan 16-31
Advances in the treatment of epilepsy.
2001 Jul 1
[West syndrome--new therapeutic approach].
2001 May-Jun
The NMDA receptor complex: a promising target for novel antiepileptic strategies.
2001 Sep
Anticonvulsant drug hypersensitivity.
2002
Antiepileptic drugs and agents that inhibit voltage-gated sodium channels prevent NMDA antagonist neurotoxicity.
2002
Anticonvulsants: aspects of their mechanisms of action.
2002
Mechanisms underlying the nociception and paw oedema caused by injection of glutamate into the mouse paw.
2002 Jan 11
P-Glycoprotein-mediated efflux of phenobarbital, lamotrigine, and felbamate at the blood-brain barrier: evidence from microdialysis experiments in rats.
2002 Jul 26
Interaction between human serum albumin and the felbamate metabolites 4-Hydroxy-5-phenyl-[1,3]oxazinan-2-one and 2-phenylpropenal.
2002 Jun
New antiepileptic drugs.
2002 Mar
Some common issues in the use of antiepileptic drugs.
2002 Mar
[New antiepileptic drugs: new therapeutic options].
2002 May
Reactivity of atropaldehyde, a felbamate metabolite in human liver tissue in vitro.
2002 Nov 10
Anticonvulsant and antiepileptogenic effects of fluorofelbamate in experimental status epilepticus.
2002 Oct
New antiepileptic drugs in childhood.
2002 Sep
Effect of antiepileptic drugs on bodyweight: overview and clinical implications for the treatment of epilepsy.
2003
Treatment of Lennox-Gastaut syndrome.
2003
Clinical care of pregnant women with epilepsy: neural tube defects and folic acid supplementation.
2003
Drug treatment of epilepsy in elderly people: focus on valproic Acid.
2003
Is the interaction between felbamate and valproate against seizures induced by 4-aminopyridine and pentylenetetrazole in mice beneficial?
2003 Aug
Influence of some convulsant agents on the protective activity of a novel antiepileptic drug, felbamate, against maximal electroshock in mice.
2003 Jul-Aug
In vivo CYP3A4 heteroactivation is a possible mechanism for the drug interaction between felbamate and carbamazepine.
2003 Jun
Interactions of tiagabine with some antiepileptics in the maximal electroshock in mice.
2003 May
Influence of felbamate on the antinociceptive action of morphine, metamizol and indomethacin in mice.
2003 May-Jun
Relationship between extent of inhibition and inhibitor dose: literature evaluation based on the metabolism and transport drug interaction database.
2003 Oct
Rapid and simple high-performance liquid chromatographic determination of felbamate in serum.
2003 Sep-Oct
Therapeutic drug monitoring of old and newer anti-epileptic drugs.
2004
Pharmacologic treatment of the catastrophic epilepsies.
2004
Preclinical profile of combinations of some second-generation antiepileptic drugs: an isobolographic analysis.
2004 Aug
Investigating the role of 2-phenylpropenal in felbamate-induced idiosyncratic drug reactions.
2004 Dec
Use-dependent inhibition of the N-methyl-D-aspartate currents by felbamate: a gating modifier with selective binding to the desensitized channels.
2004 Feb
A new linker for glucuronylated anticancer prodrugs.
2004 Feb 15
[Drug interactions with antiepileptic agents].
2004 Feb 28
The new antiepileptic drugs: scientific review.
2004 Feb 4
Effects of seven clinically important antiepileptic drugs on inhibitory glycine receptor currents in hippocampal neurons.
2004 Jan
Behavioural effects of the newer antiepileptic drugs: an update.
2004 Jan
New antiepileptic agents.
2004 Jan-Feb
Pharmacodynamic interaction studies with topiramate in the pentylenetetrazol and maximal electroshock seizure models.
2004 Jul
[Treatment protocol for long-term anti-epilepsy drugs in adults with refractory partial epilepsy].
2004 Jun
Effect of felbamate and its combinations with conventional antiepileptics in amygdala-kindled rats.
2004 May
Influence of felbamate on selected central effects of ethanol in experimental animals.
2004 May-Jun
Isobolographic and subthreshold analysis of interactions among felbamate and four conventional antiepileptic drugs in pentylenetetrazole-induced seizures in mice.
2004 Oct
Efficacy and tolerability of the new antiepileptic drugs: comparison of two recent guidelines.
2004 Oct
Significance of MDR1 and multiple drug resistance in refractory human epileptic brain.
2004 Oct 9
Progress report on new antiepileptic drugs: a summary of the Seventh Eilat Conference (EILAT VII).
2004 Sep-Oct
Mechanisms of action of antiepileptic drugs.
2005
Interaction between lamotrigine and felbamate in the maximal electroshock-induced seizures in mice: an isobolographic analysis.
2005 Mar
Patents

Sample Use Guides

In Vivo Use Guide
Adjunctive therapy: 1200 mg/day in 3-4 divided doses. The daily dose can be increased in 1200 mg increments each week as tolerated to response. Maximum daily dose: 3600 mg. Monotherapy: 1200 mg/day in 3-4 divided doses. Increase the daily dose in 600 mg increments every two weeks as tolerated to response.
Route of Administration: Oral
In Vitro Use Guide
At concentrations of 30 to 100 nM, Felbamate produced a significant inhibition of high-voltage-activated Ca++ currents (-6/-15%). At saturating concentrations (1-3 uM), Felbamate-mediated inhibition averaged 44% in rat cortical and neostriatal neurons.
Name Type Language
FELBAMATE
HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official Name English
ADD-03055
Code English
W-554
Code English
FELBAMATE [ORANGE BOOK]
Common Name English
FELBAMATE [WHO-DD]
Common Name English
CARBAMIC ACID 2-PHENYLTRIMETHYLENE ESTER
Common Name English
FELBAMATE [MI]
Common Name English
FELBAMATE [USP-RS]
Common Name English
2-PHENYL-1,3-PROPANEDIOL 1,3-DICARBAMATE
Common Name English
FELBAMATE [INN]
Common Name English
1,3-PROPANEDIOL, 2-PHENYL-, DICARBAMATE
Systematic Name English
FELBATOL
Brand Name English
FELBAMATE [VANDF]
Common Name English
FELBAMATE [USAN]
Common Name English
FELBAMATE [MART.]
Common Name English
TALOXA
Brand Name English
FELBAMATE [HSDB]
Common Name English
Classification Tree Code System Code
LIVERTOX 401
Created by admin on Tue Oct 22 00:15:17 UTC 2019 , Edited by admin on Tue Oct 22 00:15:17 UTC 2019
NCI_THESAURUS C264
Created by admin on Tue Oct 22 00:15:17 UTC 2019 , Edited by admin on Tue Oct 22 00:15:17 UTC 2019
NDF-RT N0000008486
Created by admin on Tue Oct 22 00:15:17 UTC 2019 , Edited by admin on Tue Oct 22 00:15:17 UTC 2019
NDF-RT N0000175753
Created by admin on Tue Oct 22 00:15:17 UTC 2019 , Edited by admin on Tue Oct 22 00:15:17 UTC 2019
FDA ORPHAN DRUG 33488
Created by admin on Tue Oct 22 00:15:17 UTC 2019 , Edited by admin on Tue Oct 22 00:15:17 UTC 2019
WHO-ATC N03AX10
Created by admin on Tue Oct 22 00:15:17 UTC 2019 , Edited by admin on Tue Oct 22 00:15:17 UTC 2019
WHO-VATC QN03AX10
Created by admin on Tue Oct 22 00:15:17 UTC 2019 , Edited by admin on Tue Oct 22 00:15:17 UTC 2019
Code System Code Type Description
RXCUI
24812
Created by admin on Tue Oct 22 00:15:17 UTC 2019 , Edited by admin on Tue Oct 22 00:15:17 UTC 2019
PRIMARY RxNorm
MESH
C047360
Created by admin on Tue Oct 22 00:15:17 UTC 2019 , Edited by admin on Tue Oct 22 00:15:17 UTC 2019
PRIMARY
NCI_THESAURUS
C47530
Created by admin on Tue Oct 22 00:15:17 UTC 2019 , Edited by admin on Tue Oct 22 00:15:17 UTC 2019
PRIMARY
EPA CompTox
25451-15-4
Created by admin on Tue Oct 22 00:15:17 UTC 2019 , Edited by admin on Tue Oct 22 00:15:17 UTC 2019
PRIMARY
IUPHAR
5473
Created by admin on Tue Oct 22 00:15:17 UTC 2019 , Edited by admin on Tue Oct 22 00:15:17 UTC 2019
PRIMARY
EVMPD
SUB07526MIG
Created by admin on Tue Oct 22 00:15:17 UTC 2019 , Edited by admin on Tue Oct 22 00:15:17 UTC 2019
PRIMARY
CAS
25451-15-4
Created by admin on Tue Oct 22 00:15:17 UTC 2019 , Edited by admin on Tue Oct 22 00:15:17 UTC 2019
PRIMARY
HSDB
25451-15-4
Created by admin on Tue Oct 22 00:15:17 UTC 2019 , Edited by admin on Tue Oct 22 00:15:17 UTC 2019
PRIMARY
WIKIPEDIA
FELBAMATE
Created by admin on Tue Oct 22 00:15:17 UTC 2019 , Edited by admin on Tue Oct 22 00:15:17 UTC 2019
PRIMARY
DRUG BANK
DB00949
Created by admin on Tue Oct 22 00:15:17 UTC 2019 , Edited by admin on Tue Oct 22 00:15:17 UTC 2019
PRIMARY
LactMed
25451-15-4
Created by admin on Tue Oct 22 00:15:17 UTC 2019 , Edited by admin on Tue Oct 22 00:15:17 UTC 2019
PRIMARY
MERCK INDEX
M5254
Created by admin on Tue Oct 22 00:15:17 UTC 2019 , Edited by admin on Tue Oct 22 00:15:17 UTC 2019
PRIMARY Merck Index
PUBCHEM
3331
Created by admin on Tue Oct 22 00:15:17 UTC 2019 , Edited by admin on Tue Oct 22 00:15:17 UTC 2019
PRIMARY
INN
5686
Created by admin on Tue Oct 22 00:15:17 UTC 2019 , Edited by admin on Tue Oct 22 00:15:17 UTC 2019
PRIMARY
ECHA (EC/EINECS)
247-001-4
Created by admin on Tue Oct 22 00:15:17 UTC 2019 , Edited by admin on Tue Oct 22 00:15:17 UTC 2019
PRIMARY
ChEMBL
CHEMBL1094
Created by admin on Tue Oct 22 00:15:17 UTC 2019 , Edited by admin on Tue Oct 22 00:15:17 UTC 2019
PRIMARY